Hydrochloric Acid → 4-[2-(Diethylamino)ethyl]aniline

Participants

Reaction Steps

To a solution of 2-(4-aminophenyl)-N,N-diethylacetamide, (2-NB-2-A13; 1.5 g, 7.28 mmol) from Step 2 in anhydrous THF (15 mL) kept at 0° C. was added a 2 M solution of borane dimethylsulfide in THF (14.5 mL, 29 mmol) slowly. The reaction was allowed to warm to room temperature and stirred for 18 h. Hydrochloric acid (6N, 10 mL) was carefully added and the reaction was refluxed for 1 hour followed by cooling to room temperature and neutralization with 3N sodium hydroxide solution. Aqueous layer was separated and extracted with ethyl acetate (4×30 mL). Combined organic layer was dried over sodium sulfate, filtered and evaporated to provide 4-(2-(diethylamino)ethyl)aniline as a light-brown oil (1.25 g, 86%).

Provenance & Evidence